ORGN 446 |
| Shinjiro Sumi, Koji Matsumoto, Hidetoshi Tokuyama, and Tohru Fukuyama. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan |
| Haplophytine (1) is the major alkaloid isolated from the dried leaves of the plant Haplophyton cimicidum, and aspidophytine (2) was obtained by acid hydrolysis of 1. The enantioselective total synthesis of aspidophytine (2) has been accomplished. The key indole intermediate was efficiently prepared by radical cyclization of 2-alkenylphenylisocyanide followed by Sonogashira-coupling with a highly functionalized terminal acetylene. The 11-membered cyclic amine, a precursor for the formation of the aspidosperma skeleton, was synthesized using nitrobenzenesulfonamide chemistry. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
